This doesn’t sound very convincing, mostly because the examples don’t really line up with the claim. Apple supposedly struggles “up the stack,” yet many of the best and most-used iPhone apps are built by Apple itself. Google is held up as failing at social, but YouTube is arguably the largest social network in the world. Oracle is described as struggling in apps, yet it’s clearly doing just fine as a massive, profitable enterprise software company. And the IBM example is backwards: IBM didn’t accidentally hand Microsoft the OS layer, it already had its own operating systems. In fact, Microsoft is the clearest counterexample here, it got big by owning the OS and then very successfully moved up the stack to dominate applications with Office.
I don't think anyone at Google thought building a social network would be easy, and Page knows Google planned and did spend a huge amount of money on the failure.
Google just that it was necessary and possible, not that it would be easy. I suspect that many other up-the-stack adventures by other companies were similar.
I think a lot of your examples are flawed. Google didn’t build the initial version of YouTube, they bought it.
A lot of Apple’s apps predate the App Store. The apps that came later had limited use until Apple spent a lot of time refining them. Think Apple Maps.
Microsoft released Word for Mac a year before they released Windows 1.0, so Windows was “down the stack” for them.
FWIW the article is from 2016 (although, if the article was discovering some real underlying force it shouldn’t be invalidated by the passage of time). Apple Maps was quite bad when it was released, I forget when that was exactly, but maybe it was recent enough in 2016 to be top-of-mind?